# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shi_3410_rola
_database_code_depnum_ccdc_archive 'CCDC 2008469'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi, Romania
Romania
;
_audit_update_record             
;
2020-06-07 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-10-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cu N8'
_chemical_formula_sum            'C16 H14 Cu N8'
_chemical_formula_weight         381.89
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H25 N6 O6 Cu1'
_chemical_oxdiff_usercomment     '44 CuAC2 2-1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.3383(4)
_cell_length_b                   9.0913(6)
_cell_length_c                   15.5717(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.648(6)
_cell_angle_gamma                90
_cell_volume                     752.06(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    932
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5400
_cell_measurement_theta_min      2.5850
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.757
_exptl_absorpt_coefficient_mu    1.470
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             390
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3075
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.597
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  24.00   1.00   10.00    --  -15.44 -99.00 -60.00   35
  2  ω     -9.00  82.00   1.00   10.00    --   17.71  77.00 150.00   91
  3  ω    -49.00  44.00   1.00   10.00    --   17.71 -77.00  30.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0515492000
_diffrn_orient_matrix_UB_12      -0.0398486000
_diffrn_orient_matrix_UB_13      0.0367145000
_diffrn_orient_matrix_UB_21      -0.0924901000
_diffrn_orient_matrix_UB_22      0.0303394000
_diffrn_orient_matrix_UB_23      0.0245358000
_diffrn_orient_matrix_UB_31      -0.0813400000
_diffrn_orient_matrix_UB_32      -0.0598440000
_diffrn_orient_matrix_UB_33      -0.0120018000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                997
_reflns_number_total             1336
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1065
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.000000 0.500000 0.500000 0.0309(3) Uani 1 2 d S T P . .
N1 N 0.9042(5) 0.4792(3) 0.62279(19) 0.0282(7) Uani 1 1 d . . . . .
N2 N 0.7278(5) 0.6431(3) 0.49435(17) 0.0294(7) Uani 1 1 d . . . . .
N3 N 0.6022(5) 0.7344(3) 0.43490(18) 0.0317(7) Uani 1 1 d . . . . .
N4 N 0.4038(5) 0.7359(3) 0.55665(18) 0.0312(7) Uani 1 1 d . . . . .
C1 C 1.0104(7) 0.3921(4) 0.6859(2) 0.0333(9) Uani 1 1 d . . . . .
H1 H 1.149972 0.335799 0.675862 0.040 Uiso 1 1 calc R . . . .
C2 C 0.9174(7) 0.3844(4) 0.7654(2) 0.0394(10) Uani 1 1 d . . . . .
H2 H 0.990823 0.321328 0.807689 0.047 Uiso 1 1 calc R . . . .
C3 C 0.7157(8) 0.4702(4) 0.7817(2) 0.0409(10) Uani 1 1 d . . . . .
H3 H 0.653603 0.467650 0.835441 0.049 Uiso 1 1 calc R . . . .
C4 C 0.6071(7) 0.5598(4) 0.7175(2) 0.0373(10) Uani 1 1 d . . . . .
H4 H 0.470200 0.618790 0.727022 0.045 Uiso 1 1 calc R . . . .
C5 C 0.7042(6) 0.5609(4) 0.6391(2) 0.0274(8) Uani 1 1 d . . . . .
C6 C 0.6046(6) 0.6481(4) 0.5644(2) 0.0279(8) Uani 1 1 d . . . . .
C7 C 0.4124(6) 0.7865(4) 0.4751(2) 0.0286(8) Uani 1 1 d . . . . .
C8 C 0.2289(7) 0.8957(4) 0.4341(2) 0.0383(10) Uani 1 1 d . . . . .
H8A H 0.267421 0.991604 0.457641 0.058 Uiso 1 1 calc GR . . . .
H8B H 0.061498 0.868434 0.445327 0.058 Uiso 1 1 calc GR . . . .
H8C H 0.239730 0.897419 0.372907 0.058 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.036(3) . ?
Cu1 N1 2.036(3) 3_766 ?
Cu1 N2 1.946(3) . ?
Cu1 N2 1.946(3) 3_766 ?
N1 C1 1.343(4) . ?
N1 C5 1.346(4) . ?
N2 N3 1.369(4) . ?
N2 C6 1.329(4) . ?
N3 C7 1.329(4) . ?
N4 C6 1.332(4) . ?
N4 C7 1.357(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(4) . ?
C5 C6 1.464(5) . ?
C7 C8 1.493(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 180.00(14) 3_766 . ?
N2 Cu1 N1 98.67(11) . 3_766 ?
N2 Cu1 N1 98.67(11) 3_766 . ?
N2 Cu1 N1 81.33(11) 3_766 3_766 ?
N2 Cu1 N1 81.33(11) . . ?
N2 Cu1 N2 180.0 3_766 . ?
C1 N1 Cu1 128.0(2) . . ?
C1 N1 C5 118.2(3) . . ?
C5 N1 Cu1 113.8(2) . . ?
N3 N2 Cu1 138.6(2) . . ?
C6 N2 Cu1 114.4(2) . . ?
C6 N2 N3 106.6(3) . . ?
C7 N3 N2 104.1(3) . . ?
C6 N4 C7 100.8(3) . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.6(3) . . ?
C2 C1 H1 119.2 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.7(3) . . ?
N1 C5 C6 112.4(3) . . ?
C4 C5 C6 124.9(3) . . ?
N2 C6 N4 113.9(3) . . ?
N2 C6 C5 117.6(3) . . ?
N4 C6 C5 128.5(3) . . ?
N3 C7 N4 114.7(3) . . ?
N3 C7 C8 122.3(3) . . ?
N4 C7 C8 123.0(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 N3 0.93 2.36 3.148(5) 141.9 3_766 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 C1 C2 -176.9(3) . . . . ?
Cu1 N1 C5 C4 178.6(3) . . . . ?
Cu1 N1 C5 C6 -0.9(4) . . . . ?
Cu1 N2 N3 C7 171.7(3) . . . . ?
Cu1 N2 C6 N4 -173.8(2) . . . . ?
Cu1 N2 C6 C5 7.0(4) . . . . ?
N1 C1 C2 C3 -1.8(6) . . . . ?
N1 C5 C6 N2 -3.9(4) . . . . ?
N1 C5 C6 N4 177.1(3) . . . . ?
N2 N3 C7 N4 -0.1(4) . . . . ?
N2 N3 C7 C8 178.1(3) . . . . ?
N3 N2 C6 N4 0.2(4) . . . . ?
N3 N2 C6 C5 -179.0(3) . . . . ?
C1 N1 C5 C4 0.7(5) . . . . ?
C1 N1 C5 C6 -178.9(3) . . . . ?
C1 C2 C3 C4 1.5(6) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 N1 -1.0(6) . . . . ?
C3 C4 C5 C6 178.5(3) . . . . ?
C4 C5 C6 N2 176.5(3) . . . . ?
C4 C5 C6 N4 -2.5(6) . . . . ?
C5 N1 C1 C2 0.7(5) . . . . ?
C6 N2 N3 C7 0.0(4) . . . . ?
C6 N4 C7 N3 0.2(4) . . . . ?
C6 N4 C7 C8 -177.9(3) . . . . ?
C7 N4 C6 N2 -0.3(4) . . . . ?
C7 N4 C6 C5 178.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.172
_oxdiff_exptl_absorpt_empirical_full_min 0.824
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shi_4617_rola
_database_code_depnum_ccdc_archive 'CCDC 2008470'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi, Romania
Romania
;
_audit_update_record             
;
2020-06-07 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2020-02-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H24 Cu2 N8 O6'
_chemical_formula_sum            'C20 H24 Cu2 N8 O6'
_chemical_formula_weight         599.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N8O4Cu2
_chemical_oxdiff_usercomment     3406_repeated
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.4328(6)
_cell_length_b                   7.23016(16)
_cell_length_c                   15.4337(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.996(3)
_cell_angle_gamma                90
_cell_volume                     2380.78(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3493
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      28.8320
_cell_measurement_theta_min      1.9070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.23a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6663
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.909
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00   7.00   1.00   30.00    --  -15.29  21.00 136.00   25
  2  ω     32.00  68.00   1.00   30.00    --   17.79  21.00 136.00   36
  3  ω    -31.00  46.00   1.00   30.00    --   17.79 -21.00 -29.00   77
  4  ω    -84.00 -39.00   1.00   30.00    --  -15.29-178.00 150.00   45
  5  ω    -39.00   2.00   1.00   30.00    --  -15.29 -77.00 -90.00   41
  6  ω      2.00  83.00   1.00   30.00    --   17.79  57.00-180.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0114009000
_diffrn_orient_matrix_UB_12      -0.0160858000
_diffrn_orient_matrix_UB_13      -0.0373765000
_diffrn_orient_matrix_UB_21      -0.0307876000
_diffrn_orient_matrix_UB_22      -0.0220469000
_diffrn_orient_matrix_UB_23      -0.0277752000
_diffrn_orient_matrix_UB_31      -0.0052642000
_diffrn_orient_matrix_UB_32      0.0942558000
_diffrn_orient_matrix_UB_33      -0.0128544000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1871
_reflns_number_total             2103
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.23a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.23a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.23a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0302P)²+4.2165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0754
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O005(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00C), C1(H1), C2(H2), C5(H5)
2.c Idealised Me refined as rotating group:
 C00D(H00D,H00E,H00F), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu01 Cu 0.57763(2) 0.77530(4) 0.21359(2) 0.01581(13) Uani 1 1 d . . . . .
O002 O 0.66207(9) 0.6718(2) 0.26709(13) 0.0209(4) Uani 1 1 d . . . . .
O003 O 0.61653(9) 0.3969(2) 0.24200(13) 0.0235(5) Uani 1 1 d . . . . .
N004 N 0.41262(11) 0.8493(3) 0.01463(16) 0.0193(5) Uani 1 1 d . . . . .
O005 O 0.62033(9) 1.0456(3) 0.18293(14) 0.0244(5) Uani 1 1 d . . . . .
H00A H 0.605879 1.136907 0.205467 0.037 Uiso 1 1 d R U . . .
H00B H 0.607709 1.065661 0.125475 0.037 Uiso 1 1 d R U . . .
N006 N 0.48584(11) 0.7952(3) 0.14814(16) 0.0177(5) Uani 1 1 d . . . . .
C007 C 0.66390(13) 0.4959(4) 0.26850(19) 0.0197(6) Uani 1 1 d . . . . .
N7 N 0.57674(11) 0.7110(3) 0.08410(16) 0.0183(5) Uani 1 1 d . . . . .
N8 N 0.43139(10) 0.8408(3) 0.16590(15) 0.0176(5) Uani 1 1 d . . . . .
C00A C 0.51243(15) 0.7112(4) -0.0715(2) 0.0254(7) Uani 1 1 d . . . . .
H00C H 0.473549 0.732202 -0.114327 0.030 Uiso 1 1 calc R U . . .
C00B C 0.52124(13) 0.7418(3) 0.01965(19) 0.0183(6) Uani 1 1 d . . . . .
C00C C 0.47202(13) 0.7996(3) 0.05824(18) 0.0166(6) Uani 1 1 d . . . . .
C00D C 0.32309(13) 0.9304(4) 0.0723(2) 0.0276(7) Uani 1 1 d . . . . .
H00D H 0.311560 1.028727 0.028426 0.041 Uiso 1 1 calc R U . . .
H00E H 0.319651 0.972514 0.129521 0.041 Uiso 1 1 calc R U . . .
H00F H 0.295633 0.826918 0.051186 0.041 Uiso 1 1 calc R U . . .
C1 C 0.62454(14) 0.6511(4) 0.0574(2) 0.0227(6) Uani 1 1 d . . . . .
H1 H 0.663177 0.631257 0.101030 0.027 Uiso 1 1 calc R U . . .
C2 C 0.56215(15) 0.6491(4) -0.0982(2) 0.0292(7) Uani 1 1 d . . . . .
H2 H 0.557563 0.628834 -0.159398 0.035 Uiso 1 1 calc R U . . .
C5 C 0.61849(15) 0.6176(4) -0.0327(2) 0.0291(7) Uani 1 1 d . . . . .
H5 H 0.652472 0.573859 -0.049188 0.035 Uiso 1 1 calc R U . . .
C6 C 0.38906(13) 0.8731(4) 0.08417(19) 0.0185(6) Uani 1 1 d . . . . .
C3 C 0.72776(15) 0.4093(4) 0.3044(3) 0.0366(8) Uani 1 1 d . . . . .
H3A H 0.758220 0.503357 0.330534 0.055 Uiso 1 1 calc R U . . .
H3B H 0.738212 0.349647 0.255465 0.055 Uiso 1 1 calc R U . . .
H3C H 0.727617 0.319612 0.350230 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu01 O002 1.9655(19) . ?
Cu01 O005 2.2893(19) . ?
Cu01 N006 1.999(2) . ?
Cu01 N7 2.046(2) . ?
Cu01 N8 1.989(2) 2_655 ?
O002 C007 1.273(3) . ?
O003 C007 1.241(3) . ?
N004 C00C 1.343(3) . ?
N004 C6 1.346(3) . ?
O005 H00A 0.8555 . ?
O005 H00B 0.8557 . ?
N006 N8 1.372(3) . ?
N006 C00C 1.325(4) . ?
C007 C3 1.504(4) . ?
N7 C00B 1.351(4) . ?
N7 C1 1.335(4) . ?
N8 C6 1.344(3) . ?
C00A H00C 0.9300 . ?
C00A C00B 1.376(4) . ?
C00A C2 1.379(4) . ?
C00B C00C 1.468(4) . ?
C00D H00D 0.9600 . ?
C00D H00E 0.9600 . ?
C00D H00F 0.9600 . ?
C00D C6 1.492(4) . ?
C1 H1 0.9300 . ?
C1 C5 1.376(4) . ?
C2 H2 0.9300 . ?
C2 C5 1.371(5) . ?
C5 H5 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O002 Cu01 O005 90.07(7) . . ?
O002 Cu01 N006 161.50(8) . . ?
O002 Cu01 N7 92.36(9) . . ?
O002 Cu01 N8 93.49(9) . 2_655 ?
N006 Cu01 O005 105.40(8) . . ?
N006 Cu01 N7 79.93(9) . . ?
N7 Cu01 O005 82.56(8) . . ?
N8 Cu01 O005 99.21(8) 2_655 . ?
N8 Cu01 N006 93.95(9) 2_655 . ?
N8 Cu01 N7 173.88(9) 2_655 . ?
C007 O002 Cu01 114.17(18) . . ?
C00C N004 C6 102.0(2) . . ?
Cu01 O005 H00A 109.8 . . ?
Cu01 O005 H00B 109.5 . . ?
H00A O005 H00B 104.2 . . ?
N8 N006 Cu01 139.28(18) . . ?
C00C N006 Cu01 113.71(19) . . ?
C00C N006 N8 105.6(2) . . ?
O002 C007 C3 116.4(3) . . ?
O003 C007 O002 123.4(3) . . ?
O003 C007 C3 120.2(3) . . ?
C00B N7 Cu01 114.24(18) . . ?
C1 N7 Cu01 127.5(2) . . ?
C1 N7 C00B 118.1(2) . . ?
N006 N8 Cu01 118.92(17) . 2_655 ?
C6 N8 Cu01 132.25(19) . 2_655 ?
C6 N8 N006 105.6(2) . . ?
C00B C00A H00C 120.5 . . ?
C00B C00A C2 119.0(3) . . ?
C2 C00A H00C 120.5 . . ?
N7 C00B C00A 122.3(3) . . ?
N7 C00B C00C 112.7(2) . . ?
C00A C00B C00C 124.9(3) . . ?
N004 C00C C00B 128.8(3) . . ?
N006 C00C N004 114.0(2) . . ?
N006 C00C C00B 117.1(3) . . ?
H00D C00D H00E 109.5 . . ?
H00D C00D H00F 109.5 . . ?
H00E C00D H00F 109.5 . . ?
C6 C00D H00D 109.5 . . ?
C6 C00D H00E 109.5 . . ?
C6 C00D H00F 109.5 . . ?
N7 C1 H1 118.9 . . ?
N7 C1 C5 122.1(3) . . ?
C5 C1 H1 118.9 . . ?
C00A C2 H2 120.6 . . ?
C5 C2 C00A 118.7(3) . . ?
C5 C2 H2 120.6 . . ?
C1 C5 H5 120.1 . . ?
C2 C5 C1 119.7(3) . . ?
C2 C5 H5 120.1 . . ?
N004 C6 C00D 123.8(3) . . ?
N8 C6 N004 112.9(2) . . ?
N8 C6 C00D 123.4(3) . . ?
C007 C3 H3A 109.5 . . ?
C007 C3 H3B 109.5 . . ?
C007 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu01 O002 C007 O003 -2.8(4) . . . . ?
Cu01 O002 C007 C3 177.0(2) . . . . ?
Cu01 N006 N8 Cu01 -34.6(3) . . . 2_655 ?
Cu01 N006 N8 C6 163.3(2) . . . . ?
Cu01 N006 C00C N004 -167.50(17) . . . . ?
Cu01 N006 C00C C00B 15.5(3) . . . . ?
Cu01 N7 C00B C00A 178.2(2) . . . . ?
Cu01 N7 C00B C00C -5.1(3) . . . . ?
Cu01 N7 C1 C5 -178.0(2) . . . . ?
Cu01 N8 C6 N004 -157.99(19) 2_655 . . . ?
Cu01 N8 C6 C00D 22.3(4) 2_655 . . . ?
N006 N8 C6 N004 0.7(3) . . . . ?
N006 N8 C6 C00D -179.0(2) . . . . ?
N7 C00B C00C N004 176.7(2) . . . . ?
N7 C00B C00C N006 -6.8(3) . . . . ?
N7 C1 C5 C2 1.1(4) . . . . ?
N8 N006 C00C N004 1.6(3) . . . . ?
N8 N006 C00C C00B -175.5(2) . . . . ?
C00A C00B C00C N004 -6.7(4) . . . . ?
C00A C00B C00C N006 169.8(3) . . . . ?
C00A C2 C5 C1 -1.0(4) . . . . ?
C00B N7 C1 C5 -1.0(4) . . . . ?
C00B C00A C2 C5 0.8(4) . . . . ?
C00C N004 C6 N8 0.2(3) . . . . ?
C00C N004 C6 C00D 179.9(3) . . . . ?
C00C N006 N8 Cu01 160.79(17) . . . 2_655 ?
C00C N006 N8 C6 -1.3(3) . . . . ?
C1 N7 C00B C00A 0.9(4) . . . . ?
C1 N7 C00B C00C 177.6(2) . . . . ?
C2 C00A C00B N7 -0.8(4) . . . . ?
C2 C00A C00B C00C -177.0(3) . . . . ?
C6 N004 C00C N006 -1.1(3) . . . . ?
C6 N004 C00C C00B 175.5(3) . . . . ?


_olex2_date_sample_data_collection 2020-02-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.180
_oxdiff_exptl_absorpt_empirical_full_min 0.896
